1,2-Dichloropropane is boiled with excess aqueous NaOH to complete substitution, and the organic product is treated with excess HIO4. Which pair of organic products is obtained, and how many moles of HIO4 are consumed per mole of the hydrolysis product?

ethanoic acid and methanoic acid; 2

JEE Advanced levelSingle correct optionDifficulty 3 of 3ro161

1,2-Dichloropropane is boiled with excess aqueous NaOH to complete substitution, and the organic product is treated with excess $HIO X_{4}$ . Which pair of organic products is obtained, and how many moles of $HIO X_{4}$ are consumed per mole of the hydrolysis product?

Aqueous NaOH replaces both Cl atoms, giving propane-1,2-diol,

CH X_{3} CH (OH) CH X_{2} OH

. A vicinal diol is cleaved by

HIO X_{4}

with one equivalent, breaking the C-C bond between the two carbinol carbons:

CH X_{3} CHO

from C2 and

HCHO

from C1.